


Enigmas of Family

by Apathetic_Abstract_Apotheosis



Category: Batman (Comics), Batman - All Media Types
Genre: Alternate Universe - Canon Divergence, BAMF Stephanie Brown, Canon-Typical Violence, Family Dynamics, Family Feels, Father-Daughter Relationship, Gen, Humor, Light Angst, Minor Stephanie Brown/Cassandra Cain, Riddles, Stephanie Brown-centric, not very good ones though
Language: English
Status: In-Progress
Published: 2020-12-07
Updated: 2021-02-22
Packaged: 2021-03-09 23:21:45
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 9,067
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27934540
Author URL: https://archiveofourown.org/users/Apathetic_Abstract_Apotheosis/pseuds/Apathetic_Abstract_Apotheosis
Summary: When Steph set out to spoil her father's latest plans, she did not expect to find someone else there before her. Nor did she expect to receive a job offer from the Riddler of all things. Still, it's not as though she had anything better going with Batman being all Batman as usual. Besides, there could be far worse people to work for, what was the worst thing that could happen?
Relationships: Stephanie Brown & Edward Nygma, Stephanie Brown/Cassandra Cain
Comments: 13
Kudos: 62





	1. Chapter 1

When Steph had put on her costume that evening ready for a night of spoiling her father’s plans, she had not expected to be beaten to it.

After the first few breakouts and crime sprees Cluemaster committed, Batman and the other heroes slowed down their investigations, only going after him if he did something particularly heinous and noteworthy.

Steph, on the other hand, kept a careful eye on the news, and whenever there was a breakout at Blackgate, she would comb all the news sites, checking to see if her deadbeat father was one of the escapees. Much to her annoyance, this time she was unlucky and Arthur Brown was indeed listed as one of the missing prisoners.

And so she’d donned the eggplant cape once again and headed out into the night. Thankfully, the summer break had begun the week before, so she wouldn’t be suffering the ill-effects of staying up all night the next day at school.

It was oddly liberating, leaping from rooftop to rooftop, using the few tips she’d learned from Robin before Batman had forbidden him from seeing her. Still, it was a wonderful feeling, the rush of wind through her hair as she soared.

Were this any other criminal, Spoiler would have had no leads, but after his last spate of crimes, she’d taken extra care to sift through everything that had been left behind at Cluemaster’s last hideout, and eventually she’d found a list of contacts.

Granted, it wasn’t much to go on, something proved by the first few addresses on the list being total busts. But it was better than nothing, and Steph wanted nothing more than her scumbag of a father put back behind bars where he couldn’t hurt anyone else.

It was quite the surprise when she’d made her way halfway down the list and was investigating an abandoned warehouse in the docks of Old Gotham to find her father already trussed up and beaten to nearly a pulp. It was even more of a surprise when she recognised the green-suited man standing over Cluemaster’s prone body and flanked by two women.

“Artie, Artie, Artie.” The Riddler tutted disapprovingly. “Riddle me this: what was it I told you last time you were out of Blackgate?” Steph’s father merely groaned in response and the Riddler sighed deeply. “I told you to get your own schtick and leave the puzzling to the greatest mind in Gotham.”

With another theatrical sigh, Riddler began pacing back and forth, twirling his cane whilst Spoiler got a little closer, crawling through the rafters to get a better view. “One might think you’re just as crazy as me to cross me like this, but I’ve read your files. Perfectly sane, though the fact that you didn’t listen to my warning before might suggest otherwise.”

Shaking his head, Riddler paused in his pacing to look down at Cluemaster. “I hate to do this, Artie, but I can’t have people stealing my thing. I have a reputation to uphold, and it’s hard enough getting people to take riddles seriously.” Continuing to shake his head, Riddler raised his cane like a golf club and brought it swinging down to smash into Arthur Brown’s head with a sickening crack, and the prone man went limp.

Steph’s stomach lurched at the violence as Riddler raised his cane again and smashed it into her father’s stomach. She couldn’t let this continue. No matter how much she hated her father, she couldn’t just let Riddler beat him to death.

“No!” She yelled, springing into action and dropping from the ceiling. Her shout did succeed in distracting the Riddler and his henchwomen long enough for her to land, though she’d misjudged just how far it was and she winced in pain as she hit the ground.

Not one to let a little pain stop her, Steph threw herself at the Riddler, colliding with the skinny man’s midriff and knocking them both to the floor.

“Ack!” The man yelped as Steph straddled him and cocked a fist back ready to land a solid punch on his jaw. Admittedly, this wasn’t the best plan she had ever come up with. In fact calling it a plan was rather charitable, but she needed to do something.

This impetuous proved to have been a terrible idea, as before she could punch the Riddler, her wrist was grabbed as was her other arm and she was roughly hauled off the Riddler.

“Fuck! I thought all the bats were supposed to be busy tonight!” He grumbled, crawling to his feet and straightened out his suit whilst Steph flailed madly to get free. “Since when did Artie have a sidekick?”

“I’m not his sidekick!” Steph protested hotly, trying to free herself from the henchwomen’s grip. “I hate the asshole, but I am a hero, so I can’t just let you kill him!”

“Hmmmm, no you’re not are you. You’re the Spoiler, I read about you.” His suit restored to its usual smartness, Riddler stroked his chin as he examined Spoiler closely. “Cheap material. Is this a curtain?” He plucked at the fabric of Spoiler’s cape. “From your voice and accent, I’m assuming teenage girl. Gothamite too, born and bred.”

The Riddler straightened up humming in thought as one of the henchwomen spoke up. “Uh, boss, why not just take off her mask?”

“Because there’s no fun in that, Echo.” Riddler rolled his eyes. “This is a puzzle I intend to solve without such easy clues.” He shook his head sadly as he started to pace back and forth. “Cheap materials suggest no funding from Batman or his associates. So, a normal teenage girl from Gotham who hates Cluemaster in particular.” A broad grin slid across Riddler’s face as he turned to look at Spoiler.

“A pleasure to meet you, Stephanie Brown.” Steph ceased in her struggling as the Riddler dropped into a polite bow before continuing. “You and your mother did a good job of keeping out of the news whenever Artie here got himself arrested, but I always do my research.” Riddler grinned smugly, as Steph let out a deep sigh.

“Alright, fine, you got me. You’ve metaphorically unmasked the Spoiler. Now what happens. You gonna kill me too?”

“What?!” Riddler looked aghast at the suggestion. “Who do you take me for, the Joker?”

“You were going to kill him.” Steph jerked her head behind her at her unconscious father.

“And I took no pleasure from it. It’s just business.” The Riddler rubbed at the bridge of his nose in exasperation. “And I’m not about to kill some dumb kid who stumbled upon this.”

“Hey, I’m not some dumb kid!” Steph protested hotly, starting to squirm again. “I have been stopping Cluemaster’s sorry-ass crimes ever since he started! Me being here wasn’t some accident.”

“Perhaps not.” Riddler’s expression turned pensive as he gave Steph a once over. “I hate to admit it, but Artie’s not a moron, though he barely compares to my shining intellect, of course, and it seems that the apple didn’t fall too far from the tree.”

“Uh, what?” Steph cocked her head in confusion in lieu of being able to make any visible expressions.

“Now I’m just wondering how much you could achieve with a real genius mentoring you.” Riddler continued to muse to himself, a small smirk on his face as he turned back to Steph. “Tell me, Miss Brown, how do you feel about green?”

“Okay, what the fuck?” Steph gave Riddler her best incredulous look from behind her mask. “Are you seriously about to ask me what I think you’re about to ask me?”

“Well, I could always do with more associates who are on my intellectual level. No offence, ladies.”

“Nah we get it, Eddie, we’re here for the muscle and other stuff.” The henchwoman who wasn’t Echo told Riddler.

“Exactly, and I see some promise in you, Miss Brown. A sharp mind that with training could have a chance of challenging my own.”

“You really do think very highly of yourself, don’t you?” Steph rolled her eyes. “You seriously think the girl who dresses up as a superhero to stop her asshole of a father from committing crimes is going to join up with you?”

“Well, not without the right incentives.” The Riddler smirked, leaning on his cane as he continued with his theatrics. “Just think of it as a summer internship. Just as illegal as most others, except you get paid on this one. Very generously, I might add.”

“I’m pretty sure working for a supervillain is more illegal than companies exploiting young people and flouting labour laws.” Steph pointed out and Riddler shrugged.

“Perhaps, but just think of the benefits. Good pay, I know you and your mother haven’t had it easy after the divorce, something to do with yourself over the summer, you get to spend time with one of the greatest minds in the world, and best of all, you’ll be associated with the Riddler instead of Cluemaster.”

“You lost me with the last one.”

“Just think of how embarrassing it would be if people did find out that you’re the daughter of this hack.” Riddler walked around Steph, the two henchwomen shuffling around so Steph could watch as he kicked the unconscious Cluemaster in the stomach. “Nobody would ever take you seriously. Then again, I doubt they take you seriously now anyway.”

Steph didn’t answer and instead looked away, the familiar feelings of irritation bubbling in her chest. She wouldn’t even be in this position if bat-brain would just listen to her and take Cluemaster seriously.

“If Batman or the others did take you seriously, they’d have taken you under their wing by now. But all they see you as is Cluemaster’s daughter, not worth their time or efforts.” Steph looked up to see Riddler shaking his head in sorrow. “I disagree. I see potential in you, Stephanie Brown, potential to be more than a C-tier vigilante and the daughter of some C-tier villain.”

Steph didn’t know what was weirder, the fact that the Riddler was even making this offer or that she was actually considering it just a little.

“Do I need to answer now?” She asked, surprising even herself.

“I suppose not, it is quite a big decision.” Riddler said after a moment of contemplation, then reached into his jacket and pulled out a card. “You have until… let’s say 17:00 tomorrow. Wait, is it still Tuesday?” He looked at the henchwoman who wasn’t Echo who nodded. “Excellent, it’s always good to make sure with this sort of thing.”

“Um, boss, are you sure this is a good idea?” Echo asked, looking curiously down at Steph. “Inviting a hero wannabe to our hideout and stuff.”

“I hate to say it, but I agree with her.” Steph added, unable to keep her mouth shut. “What’s to stop me from telling Batman and sending him to wherever you want me to go, and using that as my in with the bats?”

“Then it’ll have been a wasted opportunity. Not much lost on my part, just this time for the sales pitch. I suppose if I were a more boorish sort I could threaten you and your mother, but that’s not the sort of man I am.” Initially, Steph had found the Riddler’s confidence in himself rather grating, but she was getting oddly used to his smug superiority.

“Really?” Steph glanced down at her father’s still unconscious body.

“Like I said, just business with him. I’ll even sweeten the deal a little and not kill him right now.” Riddler said magnanimously, though it was punctuated with a small kick to the small of Cluemaster’s back. “But I would like you to think for a moment whether Batman will accept you even if you do lead him to my hideout.” Finished with his spiel, Riddler gestured to his henchwomen. “Let her go, ladies.”

After a moment’s hesitation, the two women complied, letting Steph flop to the floor and stagger to her feet. Standing up straight, she was presented with the small card the Riddler had fished out of his jacket earlier. “I do hope to see you tomorrow, Miss Brown. Come along, ladies, the night is still young and I feel like seeing dear Ozzy.”

With that, the Riddler turned on his heel and strutted away, his henchwomen in tow, leaving a still rather baffled Stephanie alone in the warehouse with her unconscious father.

* * *

It had taken Steph an annoyingly long time to drag her father’s unconscious body out of the warehouse and leave him somewhere where the cops could find him and take him back to Blackgate.

She’d considered staying out for a while longer, maybe see if she could find Robin and offer a hand, but her heart wasn’t really in it, so she’d returned home. When she woke up the next morning, she was half-convinced it had all been a dream, but the reports that Arthur Brown had been arrested and reimprisoned, as well as the business card tucked into her utility belt, said otherwise.

She spent a while just staring at the card, turning it over in her hand. There was nothing to really signify it had come from the Riddler, no question marks emblazoned upon it or anything like that. Several times, Steph considered contacting Robin via the emergency number he’d given her, but everytime she reached for her phone, something held her back.

Eventually, she got up from her bed and emerged into the kitchen of the small apartment she shared with her mom, lured by the smell of waffles.

“Hey, Mom, how was work?” She asked, sliding into her seat and grabbing her fork to start digging into the plate of waffles in front of her.

“Tiring, it was a long shift.” Her mom sighed, sitting down with her own plate which she picked at moodily. “And I got some bad news this morning. The landlord’s raising the rent again.”

“Oh…” Steph looked down at her waffles. They’d known this was coming for a few weeks now. The rent always went up at around this time of year, and they were already just barely scraping by.

“Don’t worry about it, it’s not your problem. I’ll just see if I can pick up some extra shifts at the hospital.” Steph’s mother reassured her, though her expression was still rather dour. The card sitting in Steph’s pocket burned as she made up her mind.

“Actually, Mom, you don’t need to do that.” Steph said slowly, trying to work out how she was going to do this whilst also pressing down the guilt that bubbled in her stomach. “Whilst you were out last night, I was doing some research and I found an internship, a paid one, that I’m a shoe-in for.”

“Oh, no, sweetie, you don’t need to do that. We’ll manage.” Steph’s mom tried to dissuade her, but Steph shook her head.

“No, I want to help, and it’s not like I had anything else planned to do this summer.” Steph shrugged, her plan already forming in her head. “I was going to do it anyway.”

“Well, if you say so…” Steph’s mom still looked unconvinced by this as Steph continued to fight off the feelings of guilt. Was she actually about to turn to a life of crime in order to help support her mother? The answer was obvious. Of course she would, she’d do anything to help out her mom.

“I need to swing by the office to let them know I’m taking the job.” Steph said, quickly shovelling the waffles into her mouth. “Better do it quickly before they hire someone else.”

“If you’re sure, dear. I suppose it would be good for you to get out of the apartment more.”

“Exactly. Love you, mom.” Steph stuffed the last of the waffles into her mouth and got up. Pressing a quick kiss to her mom’s cheek, Steph rushed back into her room to get dressed and look up how to get to the address the Riddler had given to her.

A few moments later she was ready to go, and with a wave to her mother, Steph left the apartment and headed downstairs, taking the steps two at a time. Stepping out into the bright summer sun and trying not to breathe too deeply, lest she smell the garbage that became more pungent during the summer months, Steph started towards the local subway station.

The address Riddler had given her was in Burnley, which wasn’t too far away from the apartment, but Steph didn’t really feel like walking today. It took her a little time to find the building, which for all intents and purposes looked like a normal residential brownstone.

She’d half expected some abandoned building like the one she’d found her father in last night, but then again, the Riddler was a far more successful villain and could clearly afford better premises. Shaking her head, Steph walked up to the front door and pressed the button on the intercom. It buzzed and after a moment, a sharp voice spoke from it, which Steph recognised as belonging to one of the henchwomen from last night.

“Who is it?”

“Stephanie Brown. I’m here to talk to Mr Nygma about the ‘internship’.” Steph waited anxiously for a moment before the voice crackled over the speaker, sounding more than a little nonplussed.

“Come on up.”

**Notes for the Chapter:**

> So, first venture into another new fandom and stepping out of my comfort zone with this. Hopefully you all like this and where it's going. 
> 
> I've set up a [discord](https://discord.gg/4t3y25e) so feel free to join and stuff, I'm pretty active there these days.
> 
> Big thanks to [machiavellianFictionist](https://archiveofourown.org/users/machiavellianFictionist) for proofreading and being super amazing. Lots of thanks too to my lovely girlfriend [Ruby](https://archiveofourown.org/users/RubyAndNanaAO3) for beta reading and being such a wonderful girlfriend.
> 
> Thank you too to my official supporters, send a PM or hop on the discord server for details.


	2. Chapter 2

The building’s foyer was surprisingly empty, but then again, she doubted anyone but the Riddler owned these premises. It all looked normal enough, but when she glanced back at the door as it swung shut behind her, she could tell that all those locks on it were far from standard.

The Riddler seemed to have a taste for old school design, all wood panelling in the empty room and an old style cage lift which had the staircase wrapped around it. Steph wasn’t quite sure she trusted the rickety looking contraption and opted to take the stairs instead, up past several clearly uninhabited floors until she reached one with a door labelled as ‘Enigmatic Puzzles LLC’, through which Steph could see there was a light on.

After considering for a moment whether to knock or not, Steph decided it was pointless and simply entered the room. For some reason, it was made up to be exactly like a secretary’s office, and sitting behind the desk was a tall blonde woman who had her feet propped up on the desk as she flipped through a magazine.

“He’s waiting for you, just through there.” She said in a bored tone, gesturing vaguely at the door on the opposite side of the room, not bothering to look up from her magazine.

Rolling her eyes at the woman’s lack of attention, Steph crossed the room and opened the door to reveal a large wooden desk covered in pieces of plastic and metal. Sitting behind it and fiddling with some of the pieces was the Riddler. It took Steph a moment to recognise him without the green hat and purple domino mask.

“Ah, Miss Brown, good of you to finally show up.” He gestured for her to sit in one of the chairs in front of his desk as he abandoned what he was doing and steepled his fingers.

“Yeah, well, I had to give my mom some reason for going out.” Steph defended herself as she sat down and looked curiously at the man sitting opposite her. If she’d just run into him on the street, she would never have guessed that he was one of Gotham’s most infamous criminals. In his rumpled white shirt and square glasses, he looked for all intents and purposes like any other office worker.

“Of course, of course.” The Riddler adjusted his glasses and started shoving the chaos on his desk aside. “Given the fact that Batman hasn’t come and knocked down my door yet, I take it you’d like to take me up on my offer of employment.”

“Well, it’s not like I’ve got much else to do with myself.” Steph shrugged. “And there’s far worse people I could be working for.”

“That is true. Imagine being one of those poor kids fighting over a Disney internship.” The Riddler shuddered. “Anyway, there’s quite a bit of paperwork we need to get out of the way before we have you baffling the minds of Gotham’s finest.”

“What?” Steph blinked in surprise. “Paperwork?”

“Well, of course.” The riddler gave Steph a condescending look. “You’re a smart girl, Miss Brown, I’m sure you understand how important it is for the money my organisation acquires to look legitimate.”

“I’ll be honest, I kinda assumed you just spent it at places where they don’t care how dirty the money is, like black market arms dealers or whatever.” Steph admitted. She may have a criminal for a father, but that didn’t mean she knew the ins and outs of how Gotham’s criminals’ finances worked.

“Well, I suppose, to be fair, that is how people like the Joker operate, but only because he can’t be bothered to launder his money correctly, and even he’s not crazy enough to go up against the IRS.” Riddler shook his head in irritation. “But no, I run a tight organisation here, and it’s bad for my reputation if the tax people come knocking on my henchmen’s doors for tax evasion.”

“Is that why this office belongs to ‘Enigmatic Puzzles LLC’?” Steph asked, putting air quotes around the company name. “Because I’ve got to say, did you really have to pick a name that’s so obviously linked back to you?”

“Please, Victor owns half the ice cream shops in Gotham to launder his funds.” Riddler snorted, waving his hand dismissively. “No, I have a far more diverse portfolio than just these particular holdings, but for the purposes of your ‘internship’, you will be employed by Enigmatic Puzzles.”

“And it’s all above board, is it?” Steph raised an eyebrow.

“As far as the tax man is concerned, yes.” Riddler smirked. “I trust I don’t need to go through how money laundering works with you, otherwise I might have made the wrong choice of apprentice.”

“I know how money laundering works.” Steph said irritably, remembering that project she’d done for school on how Gotham’s criminal enterprises used most of the businesses in Gotham to launder their money. It had only earned her a B too.

“Good. Just so you’re clear on what it is you’re doing on paper, you’re working for Enigmatic Puzzles LLC as an intern in our R&D department.” The Riddler reached into a drawer on his desk and pulled out a contract which he slid over the desk to Steph. “That said, if you do have any ideas for brainteasers we can manufacture, please do share them and I’ll throw in a bonus.”

“Wait, you mean this company actually makes puzzles?” Steph asked as she started to read over the contract.

“Of course. How do you think I relax after a hard day of bank robbery and confounding Batman?” The Riddler asked with a smirk. “Enigmatic Puzzles is the parent company of the Toybox. We need some reason to reinvest all that money we make selling all those toys.” Steph’s jaw dropped.

“You’re kidding me, right?” She asked, now completely ignoring the contract she’d just been looking over. “You’re telling me that you own one of the largest toy store franchises on the East coast and you’re still a supervillain?!”

“Technically, the company is owned by a Mr Eduardo Ropecabezas.” Riddler pointed out, before shaking his head. “Look, I’m not going to go into the legal complexities of my many shell companies I created in order to legitimise my criminal activities. Just sign the damn contract.”

“In a second.” Steph grumbled, continuing to read through the papers he’d handed her. “I’m not about to sign something without first reading it all the way through.” Rolling her eyes, Steph looked over the contract as Riddler sighed deeply.

“You know, that’s not actually a description of what you’re doing, it’s just for various records and things in case we get audited.” Riddler pointed out, and Steph sighed as well.

“It still could end up being a legally binding document. Not that I don’t trust you to put something in here that’s not on the up and up, but I don’t trust you.” Steph lowered the paper to look the Riddler in the eye. “I would have thought that you’d want someone who thought things through critically as your ‘apprentice’.”

“A valid point.” Riddler conceded, sitting back in his chair. “Carry on.” With Riddler’s blessing, Steph resumed her reading of the document until she reached the subject of remuneration.

“Um, you said that this was for official records, right?” Riddler nodded, already fiddling with his pieces again. “So that would mean that this is actually how much you’re going to pay me.” Again the Riddler nodded. “This is way more than interns are normally paid. Like, way, way more.”

“I am aware.” The Riddler smirked. “Enigmatic Puzzles is one of the foremost designers of puzzles and brainteasers, and we pay our employees very well.”

“Your employees being who? Me and your two henchwomen?”

“We also offer competitive rates to our many short-term contractors.” The Riddler’s grin frew only wider as he steepled his fingers. “Including various health benefits for bat-related injuries and paying for legal fees.”

“Wow, if I didn’t know who you really were, I could’ve sworn this was a legitimate business.” She hated to say it, but Steph was actually mildly impressed with the forethought Riddler had put into his operation.

“I am a professional, and fooling the police and their financial crimes division, thus proving my intellectual superiority, is an amusing diversion.” Riddler shrugged. “Now, are you going to sign or not?”

“Yeah, yeah. Just gimme a sec and a pen.” Steph grumbled, skimming through the last page. Nothing seemed out of the ordinary, aside from the fact that Steph knew the contract was completely bogus to begin with.

Taking the pen the Riddler offered, Steph signed her name on the dotted line and dated the contract before handing it back to the Riddler for him to countersign.

“Excellent, Welcome on board, Ms Brown.” Signing the papers with a flourish, the Riddler opened up the drawer and stuffed the contract into it before getting to his feet and straightening out his shirt. “I’ll file that properly later, right now we have other important things to do.”

“Like what?” Steph asked, following suit.

“Well, firstly, I need to introduce you to the rest of the team and get you matching with the dress code, as well as a name, and all of that’s before I even get started on training you.” Riddler reeled off as he walked around the desk, picking up an offensively plain brown suit jacket from the coat stand as he went.

“Hold on, training?” Steph asked incredulously, following her new employer as he walked to the door. “Nobody said anything about training.”

“What part of ‘apprentice’ did you not understand?” The Riddler paused before opening the door. “You have a natural aptitude and intellect, but it still needs honing before it can even begin to be matched against Batman and the others. Thus, training.”

“Right…” Steph wasn’t entirely sold on this, but she was forced to run after Riddler as he left the room. He didn’t go very far as he stopped in front of his blonde henchwoman.

“Dierdre, I’d like to introduce you to the newest member of our little organisation.” The henchwoman finally took notice of Steph as she lowered her magazine and looked at her in surprise.

“You actually hired her, boss?” She asked incredulously, looking between Steph and the Riddler. “I thought you were just joking.”

“Dierdre, you should know by now that I don’t joke about things like that.” The Riddler shook his head in disappointment.

“Yeah, well, just so long as she’s not getting paid more than me or Nina, we’re good.” Diedre shrugged, returning her attention to her magazine.

“You’re welcome to discuss your salaries at a later date, right now we have an appointment with the tailor.” Riddler gave Dierdre a charming smile before walking towards the exit of the offices. “We need to get Miss Brown something more suitable to wear.”

“I really hope you’re not going to dress her up in fishnets like you got me and Nina to do.” Dierdre gave Riddler a disapproving look. “She’s only like fifteen.”

“Sixteen, actually.” Steph corrected, though she gave the Riddler a hard look. “And there’d better be no fishnets. Do I look like Black Canary?”

“Of course there’ll be no fishnets.” The Riddler groaned, pausing with his hand on the doorknob. “You’d probably pull them off about as badly as I would. No, we’re getting you a nice tailored suit, and before you ask, yes, it will be a woman’s cut.” The man rolled his eyes as he opened the door. “What is with you people and doubting me?”

“You used to wear a bright green unitard covered in question marks.” Steph pointed out, and Dierdre had to stifle a laugh at the look on the Riddler’s face.

“We do not mention that regrettable phase.” He hissed as he blushed furiously. “Besides, Ozzy said it looked rather flattering.”

“Well, if Ozzy said so, it must be true.” Dierdre snickered, holding up her hands in surrender as the Riddler gave her a look.

“Come on, we’re wasting valuable time. Dierdre, if you could tell Nina about your new coworker and start sorting her out with all the passwords.” Riddler grumbled, leading the way out of the offices with Steph following dutifully after him.

“You know, you seem to be putting a lot of trust in someone who’s a known associate of the batfamily.” Steph said in an awkward attempt to restart conversation. “As far as you know, I might be trying to gain your trust and greater access to your operations. Not that I am, of course.” She added hastily as the Riddler gave her a look.

“Of course such a thought occurred to me, which is why you aren’t getting full access. A necessary precaution, you understand. But more importantly, I know you, Miss Brown, or at least I know the sort of person you are.” Steph frowned at this. She didn’t like the idea of the Riddler claiming that she knew her that well.

“And what sort of person is that?”

“You’re impulsive, and wouldn’t have the patience for something like an undercover operation like this.” The Riddler explained nonchalantly as they walked down the stairs. “The current Robin, on the other hand? Something like that would be right up his alley.”

Steph’s stomach twisted uncomfortably at the mention of her sometimes-boyfriend. That was definitely a conversation that they’d need to have at a later date, if she ever decided to don the Spoiler outfit again, that was.

“I feel like I should be offended by that.” She said after an expectant silence, earning a small chuckled from the Riddler.

“Think of it as something to improve upon. Patience is a valuable asset.” They’d reached the ground floor by now and were just about to leave the building when a thought occurred to Steph.

“Um, since we’re going out in public and you’re all...” She gestured to the Riddler’s nauseatingly boring attire. “I don’t think calling you Riddler is going to be particularly useful, nor is Mr Nygma.”

“No, you’re quite right.” The Riddler hummed in thought, stroking his chin. “I suppose whilst we are incognito, you can refer to me as Mr Nashton.”

“Alright, then.” Steph nodded in agreement, and with that, Riddler opened up the door and led the way out into the heat of the Gotham summer. “So we’re going to see a tailor, then?”

“Yes, he does all the outfits for people in our line of work, and there is absolutely no way I am letting you run around in that thing you call a costume any more. I’m surprised mr rich and brooding let you out in that thing.”

“He never ‘let’ me out.” Steph huffed, having to jog a little in order to keep up with the Riddler’s long strides. “Nor did he ‘let’ me do anything. That jerk made no secret of how much he disapproved of me.”

“Yet you still went out night after night.” Riddler actually sounded mildly approving of her as they dodged around the foot traffic, heading towards the subway station. “You have conviction. I admire that. Though it is bordering on recklessness for you to wear a curtain for a cape.”

“I made the best of what I had.” Steph shrugged. She was actually rather proud of her Spoiler outfit, it had taken her ages to learn how to sew and get it right.

“Well, I still think it’s rather irresponsible for the bat not to outfit you when you made it clear that you were going to do things with or without his approval.” Stephanie had to stifle a laugh at how indignant the Riddler sounded on her behalf. It was surreal to say the least, to have a supervillain be annoyed at Batman for not taking responsibility for her safety.

“In any case, you can rest assured that I do not intend to spare any expense on your equipment, Miss Brown.” He finished with a haughty sniff, which he appeared to regret as they were just passing one of the many overflowing dumpsters in this part of town.

“Right…” Their conversation came to a brief halt as they descended into the subway, and Steph was mildly surprised that the Riddler didn’t just jump the turnstiles and instead scanned a card before passing through the barriers.

“Do you have any idea how embarrassing it would be if I were caught by transport police for not buying a ticket?” He asked Steph when he noticed her incredulous look. “I’d be laughed out of Gotham.”

Steph just nodded solemnly and bit her tongue to stop herself from laughing as Riddler took another flight of stairs down to the downtown line. Soon they were on the train being jostled and shoved around by the passengers, and Steph had to wonder how they’d react if they knew the person whose feet they were treading on was a supervillain.

“Is there a reason we’re taking the subway and not a cab?” Steph asked as she was elbowed in the side of the head for the third time. “I would have expected you to at least cough up a cab fare, or to have a car.”

“Harder to be tracked this way, and the tailor does not need any unwanted attention brought to him.” The Riddler explained patiently. “He tries to stay away from that side of our business.”

“I see…” At the mention of the tailor, something else occurred to Stephanie, something that the Riddler had said just before they left the office. “Why did you specify that this suit I was going to get would be a women's cut?”

“Well, because…” The Riddler gestured at her as best as he could in the cramped carriage. “You know, in case you thought I was being insensitive or something about your… status.”

“Wow, that has got to be possibly the most awkward way anyone has ever phrased that.” Steph snorted with laughter, getting even more amused by how incensed the Riddler looked at her reaction.

“I’m trying to be a half-decent employer here.” He grumbled, folding his arms and stumbling as the carriage rounded a corner. “So excuse me for trying to make you feel welcome.”

“You’re good, you’re good.” Steph reassured the man, still giggling. “I appreciate the thought, and I’m sure I’ll be in good hands with this tailor guy.”

“He’s the best at what he does.” The Riddler confirmed, mollified by Steph’s reassurances. “We get off at the next stop.”

“Great. I wonder if he does work in eggplant…”

**Notes for the Chapter:**

> Steph meets the wonderful world of making the funds from your criminal enterprises look legal. Oh, also just to clear things up a little about the timeline stuff, I'm setting this a little after No Man's Land, so for the purposes of this Tim is Robin and Cass is Batgirl as she should be. 
> 
> I've set up a [discord](https://discord.gg/4t3y25e) so feel free to join and stuff, I'm pretty active there these days.
> 
> Big thanks to [machiavellianFictionist](https://archiveofourown.org/users/machiavellianFictionist) for proofreading and being hella cute. Lots of thanks too to my lovely girlfriend [Ruby](https://archiveofourown.org/users/RubyAndNanaAO3) for beta reading and stopping Nana from being too mean about Steph.
> 
> Thank you too to my official supporters, send a PM or hop on the discord server for details.


	3. Chapter 3

Much like the Riddler’s office, the Tailor’s workshop was not what Steph had expected.

“It’s literally just a tailor.” She said, trying not to sound disappointed as she looked at the shopfront, whilst the Riddler snorted.

“Of course it is. What were you expecting?”

“I don’t know, something a bit less obvious for the guy who apparently makes all the costumes for Gotham’s rogues?” Steph wondered for a moment whether her father had ever paid a visit here. Probably not, the cheapskate almost certainly made his own costume to save on costs.

“Making our costumes isn’t his only business, you know.” Riddler sighed, leading the way to the door. “As I said before, we need various ways to make our money look legitimate, and he was a regular tailor before Ozzy commissioned him.”

Slightly hesitantly, Steph followed the Riddler into the shop, the doorbell jingling as the door opened and shut behind them and a voice called out from the backroom. “I’ll be there in a moment!” Whilst waiting, Steph had a look around the store. It was fairly small with only a few things on display, all out of Steph’s usual price range, but Steph was fairly certain that this was the sort of establishment that didn’t need big displays, given its clientele.

There was a bustling from the backroom, and a well-dressed and spindly man sporting a pair of glasses balanced precariously on the end of his nose emerged, breaking into a smile as he saw the Riddler.

“Ah, Mr Nashton, here for a new suit or repairs?” He asked in a surprisingly jovial voice for someone about to do work for a known criminal.

“A new suit, but not for me.” The Riddler stepped aside to allow Steph to approach the Tailor, whose eyes widened at the sight of her, before he gave the Riddler a hard look.

“Really, Edward? You of all people are recruiting a child to do your dirty work?” Both Steph and the Riddler protested at the same time, talking over each other.

“I’m not a child, I’m sixteen!”

“She was already going out to fight crime wearing a curtain!” They both stopped and glared at each other whilst the Tailor looked between the two.

“Are you seriously going to keep holding the curtain thing against me?” Steph demanded. “I’m poor, okay? I did the best with what I could get.”

“The fact that you used to go out in a curtain is exactly why I brought you here in the first place!” Riddler pointed out in annoyance, and Steph was about to protest further, but she was interrupted by the Tailor.

“You used to fight crime wearing a curtain?!” He sounded absolutely appalled by this and Steph blushed a little.

“It wasn’t as though I was only wearing a curtain.” She mumbled shame-facedly as the Tailor shook his head.

“I take it back, Edward, you could not have brought her to me sooner. And I suppose if she’s foolish enough to go out and fight crime without support from Batman or his associates, working for you is a lot safer. At least this way she’s less likely to get shot by some thugs.” The Tailor said, though he continued to shake his head disapprovingly.

“How do you know I didn’t get any support from Batbrain?”

“Have you not seen Batman’s costume? Or those of his associates?” The Tailor asked, raising his eyebrows. “They are works of art, using cutting-edge materials I could only dream of working with. With this lot I have to stick to things I can acquire commercially.”

“I see…” Steph hadn’t really paid much attention to Robin’s costume to know it was that fancy, but she did know it was a lot better than her attempts.

“Anyway, Arnie, we need to get Miss Brown here fitted for a suit with all the extras.” The Riddler cut in, eager to get back to business.

“And what are ‘all the extras’?” Steph asked. If she was going to be the one to wear this thing, she wanted to know what exactly it was.

“Oh the usual, bulletproof and stab-proof lining, secret pockets, a slightly roomier cut on the jacket to allow for a shoulder holster...” Steph blanched a little at the thought of carrying and using a gun. “Lockpicks sewn into the lining too, as well as a few other useful things. Oh, and my personal favourite, razorblades under the lapel.” The Tailor listed off the features as he started taking notes on a piece of paper, whilst Steph raised an eyebrow at the last one.

“You’d be surprised how many people think grabbing you by the lapels is a good idea.” The Riddler explained, carefully folding back the lapel of his jacket to show off a row of blades just underneath. “These’ll make them think twice about trying something like that.”

“I take it she’ll be wanting gloves as well.” Arnie asked, looking up from his notes.

“Of course, weighted knuckles, as usual.” Riddler confirmed before looking Steph over. “Shoes to match the suit as well, the reinforced ones.”

“He’s a glover and cobbler too?” Steph asked in amusement as Arnie raised an eyebrow at her.

“Hatter as well, but don’t tell Jervis, or he’ll have my head.” He added, making a small note. “Makes far more sense to have just one person to go to for all your costuming needs, and it means I make more money.” Really, Steph shouldn’t have been surprised that the Tailor’s main motivation for doing this sort of work was money. He probably made a lot out of it.

“I think that’s pretty much all she’s going to need… Oh and don’t forget a bowler as well, got to keep the aesthetic.”

“You and your aesthetic, Edward.” Arnie rolled his eyes good-naturedly as he finished writing. “Well, let’s get Miss Brown measured up, and then I can start pricing things for you. If you’d follow me.” He gestured for Steph to follow him into the backroom, but Steph made no move to.

“Hold on, you’re going to be the one measuring me?” Steph asked incredulously.

“Well, of course, I am the one who’ll be making the suit for you.”

“Don’t you have, I don’t know, a woman who can do it for you? Like, how do the Sirens get their costumes?” Steph asked, more than a little awkward.

“Ivy makes her own clothes, whilst Harley and Catwoman come here.” Arnie shrugged. “I assure you, Miss Brown, I’m a professional, and if there was any untoward conduct, pretty much every rogue in the city would want a piece of me.”

“If it makes you too uncomfortable, we can always go find someone else to measure you and bring those back for Arnie.” Riddler suggested, but Steph shook her head. It was kind of him to suggest it, but she didn’t want to put him through even more trouble, not when he was giving her a job and paying for all of this out of his own pocket.

“No, I’ll be fine.” She said quickly, walking over to join Arnie. “It’ll only be a sec, right?”

“Of course.” The Tailor reassured her before leading the way into the back whilst the Riddler stayed behind. The back room was filled with bolts of cloth and all sorts of other tailor’s equipment that Steph had no idea of what they were. When she’d made her own costume, it had just been whatever scraps of cloth she could scrounge up and stitch together with clumsy needlework.

“If you wouldn’t mind removing your blouse and jeans, Miss Brown, I’ll try to make this as quick as possible.” Nodding and steeling herself, Steph undid the buttons of her blouse and set it aside before doing the same with her jeans leaving her in just a bra and boxers. She felt rather awkward and vulnerable, but the Tailor said nothing, instead quickly and efficiently moving around Steph and taking her measurements before jotting them on his piece of paper.

He was finished mercifully quickly, and Steph gratefully redressed, thankful that the man had been true to his word. Once she was dressed, she was ready to return to the main part of the store, but halted at a gesture from the Tailor.

“There are a few other measurements I need, but I thought the less time you spent unclothed, the more comfortable you’d be.” Steph was rather surprised by just how considerate and courteous all these people were. Her only real experience with criminals was her father, and he was a real piece of work, a far cry from the Riddler and his associates. Hell, they were even politer than Batman was, the broody and grumpy git.

“Oh, of course. Thank you.” Arnie inclined his head before taking his tape measure and wrapping it around her head, presumably for the hat Riddler would insist upon her wearing. As he worked, he started to make light conversation about what she might like for the outfit in terms of personal touches.

“Edward is rather particular about the colours, you know what these rogues are like with their brands, but did you have any preference for the primary colours of the outfit?” He asked as he started measuring her hands.

“Um, if it’s not too much trouble, I would appreciate it if you could make the jacket and trousers in eggplant.” She suggested and the Tailor nodded, making a note of it.

“I’m sure Edward will be amenable to that. The waistcoat in purple as well?”

“Yes, please, though I’ll defer to your expertise, since I trust you know more about fashion and colour matching than I do.” She said, a little bemused by the proceedings.

“I daresay you’re most likely correct. If only the other rogues would take my advice.” Arnie sighed as he gestured for her to remove her shoes. “Some of them have reasonable enough tastes, you can’t really go wrong with a tuxedo like Oswald does, but some of them are just so outlandish. You have no idea how ridiculous a two-tone suit split down the middle looks.”

“I think I have some idea.” Steph had seen Two-Face on the news and had in the past wondered who made his odd suits.

“Yes, well, Edward isn’t much better, but at least he’s amenable to suggestions, and there are worse colour palettes than green and purple.” The Tailor continued as he finished up measuring Steph’s feet. “Oh, I assume you’re fine with green as the accent colour?”

“I doubt Mr Nygma would accept anything else.” Steph grinned wryly as the Tailor stifled a snort.

“I doubt he would.” He agreed standing up. “I believe that’s everything I need from you, Miss Brown.”

“Great, thanks.” Steph followed Arnie back to the front of the shop, where the Riddler was waiting for them, fiddling with his phone.

“All measured?” He asked when he noticed they’d returned.

“Yes, I just need to run the numbers and get you a price.” The Tailor told him, continuing to scribble out notes on his piece of paper.

“Excellent. Once we’ve sorted that out, we need to get you a cane as well.” The Riddler told Steph as she rejoined him on the other side of the counter.

“Really?” Steph raised an eyebrow. “I’m not an old lady or an English gentleman.”

“Obviously, but I think you’ll make better use of it than I will, given your…” He gestured towards Steph’s arms. “Greater propensity for physical altercations. Just think of it as a short staff, or a long club.”

“Okay, I guess that makes sense.” Steph admitted, it would be nice to have a weapon she could carry around instead of having to make do with whatever bricks and things she could find. “So what, do we need to visit a cane shop or something?”

“Of course not. I make them myself, meaning I can hide all sorts of fun tricks inside.” The Riddler scoffed as Arnie finished with his scribblings and handed over a piece of paper to the rogue.

“Here, that’s the cost for the materials and the labour. Payment in the usual way.” Glancing over the paper, the Riddler nodded and tucked it into an inside pocket of his jacket before Steph could read it.

“Hey, how much was that?” She asked, ready to start pawing at the man’s jacket, but he shook his head.

“Let me worry about the cost, Miss Brown, and if you think it’s too much, consider it my investment in you as my apprentice.” He told her, wagging his finger before looking back to the Tailor. “Could I get them done as a rush job, Arnie?”

“Let me check if I’ve got the time, I’m expecting Black Mask and some of his lieutenants this evening.” He grabbed a battered day planner and flipped it open, scanning through. “Yep, he’s coming in later on, but I can get it done in time for the day after tomorrow.”

“That’ll be fine. The usual rush job rate?” The Tailor nodded. “Excellent. Thank you for your assistance, Arnie, I’ll send either Dierdre or Nina round to pick it up when it’s done.” With a respectful nod, the Riddler turned on his heel and left the building, Steph hot on his heels after she waved goodbye to the Tailor.

“Excellent, onto our next destination.” The Riddler declared leading the way back towards the metro station. “The armoury. Well, not  _ the _ armoury, one of several.” He clarified as they descended the steps. “We’ll get you some gear, and then all you’ll need is a bit of brain training and you’ll be all set to head out on jobs.”

“Wonderful.” Steph snarked as she scanned through the barriers. “What are you going to make me do? Read a bunch of textbooks?”

“It would be a start.” The Riddler didn’t really seem to be paying attention to Steph as he led the way to the line that would take them towards the docks. Sighing, Steph followed after him, wondering exactly what he had in store for her at this armoury.

* * *

“Okay, now this is the sort of thing I was expecting.” Steph said after several long minutes of walking through the warehouses along the dockside before they finally reached a rather battered and derelict looking one. “This is the sort of place I expected rogues to make their base.”

“It is supposed to be a workshop as well as a storage facility. It doesn’t need to look nice.” The Riddler sniffed as he approached the door and unlocked it. They didn’t have to walk too far inside before Steph found that it was a lot more than met the eye from the outside. They’d entered a small room with a much larger and far more secure looking door, complete with several electronic locks.

“Just give me a few seconds.” Riddler told her as he started to open the various locks and safeguards.

“I hope your henchwomen don’t have to learn how to open these things, it must be a nightmare to remember all those codes.” Steph quipped as the Riddler went about entering various codes and inserting keys.

“Only I have access to my workshops. If I need them to help me carry something out, I unlock it for them. Security is very important. If one of them could get this door open, practically anyone could.” The Riddler answered, not bothering to look back to see Steph roll her eyes. He really was very arrogant about his own intellect. It actually made Steph want to try and break into this place later just to show him how smart she was and that she didn’t need any of his ‘brain training’.

“And here we go.” He announced as he finished unlocking the door and pushed it open, leading the way inside. Still rather irked by the man’s high opinion of himself, Steph trotted in after and found herself actually rather impressed by the room she found herself in.

All sorts of power tools lined the walls, from lathes to what looked like a 3-D printer next to a large computer setup. A large desk sat in the middle of the room and was covered with what looked like blueprints and schematics for all sorts of devices.

And lined up against the far wall was a veritable arsenal of weapons, from a wide variety of guns to more esoteric items, including several of the Riddler’s trademark question mark-topped canes. In fact, after what the Riddler had told her about the various legal loopholes and how the villains kept their money looking clean, it wouldn’t surprise Steph at all if he had trademarked the cane.

“What are all the guns for?” She asked as the Riddler marched over to the array of weapons. “I thought you weren’t that sort of rogue.”

“I’m not, they’re mostly for Nina and Dierdre, and only a fool wouldn’t resort to such methods.” The Riddler paused in his walk and looked back at Steph. “I don’t like killing, I find it rather distasteful. But when it comes down to it, I’d much rather be a living coward with a gun than a dead fool without one.”

Steph wasn’t quite sure she agreed with the Riddler’s philosophy on the usage of guns, but she didn’t question it as he ran his hands over the canes hanging on the wall, humming to himself.

“Hmmm, this one, I think.” He said after a while, selecting one and turning to Steph to toss it to her. “I think it will suit your more… hands on approach.”

Steph caught the cane from the air and was surprised by the weight of it. She gave it a few spins, remembering Robin’s lessons on how to use a bo staff, only to find it wasn’t exactly balanced. Most of the weight was in the question mark top.

“Rather heavy, isn’t it?” She asked as she gave it a few practice swings.

“I’d expect it would be given it’s got a metal core, solid aluminium. The wood on the outside is just for looks and grip.” The Riddler told her, already moving off to start looking through more of his arsenal. Stephanie continued to play with the cane for a little while. Surprisingly, it was already starting to feel comfortable in her hands.

**Notes for the Chapter:**

> I can never remember if there actually exists a tailor for all the villains in canon or if it's just a fever dream I had once. Either way, I love the concept of these perfectly ordinary people who do this sort of work on the side for the Gotham rogues because they pay a lot and someone has to make all those costumes.
> 
> I've set up a [discord](https://discord.gg/4t3y25e) so feel free to join and stuff, I'm pretty active there these days.
> 
> Big thanks to [machiavellianFictionist](https://archiveofourown.org/users/machiavellianFictionist) for proofreading and being the best at it. Lots of thanks too to my lovely girlfriend [Ruby](https://archiveofourown.org/users/RubyAndNanaAO3) for beta reading and encouraging this project.
> 
> Thank you too to my official supporters, send a PM or hop on the discord server for details.


End file.
